Azolylmethyloxiranes, use thereof for controlling plant pathogenic fungi, and agents containing the same

ABSTRACT

The present invention relates to azolylmethyloxiranes of the general formula I 
                         
in which
     A or B is benzodioxolyl which is optionally substituted by one to five of the following substituents: halogen, CN, NO 2 , amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, thio or C 1 -C 4 -alkylthio,
 
and the respective other substituent
   A or B is phenyl or 5-membered or 6-membered heteroaryl, these substituents optionally being substituted by one to three of the following substituents: halogen, CN, NO 2 , amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, thio or C 1 -C 4 -alkylthio,
 
and to the plant-compatible acid addition salts or metal salts thereof, to the use of the compounds of the formula I for controlling phytopathogenic fungi and to compositions comprising these compounds.

This application is a National Stage application of InternationalApplication No. PCT/EP2007/057353 filed Jul. 17, 2007, the entirecontents of which is hereby incorporated herein by reference. Thisapplication also claims the benefit under 35 U.S.C. §119 of EuropeanPatent Application No. 06117788.7, filed Jul. 25, 2006, the entirecontents of which is hereby incorporated herein by reference.

The present invention relates to azolylmethyloxiranes of the generalformula I

in which

-   A or B is benzodioxolyl which is optionally substituted by one to    five of the following substituents: halogen, CN, NO₂, amino,    C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy,    C₁-C₄-alkylamino, C₁-C₄-dialkylamino, thio or C₁-C₄-alkylthio,    and the respective other substituent-   A or B is phenyl or 5-membered or 6-membered heteroaryl, these    substituents optionally being substituted by one to three of the    following substituents: halogen, CN, NO₂, amino, C₁-C₄-alkyl,    C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-alkylamino,    C₁-C₄-dialkylamino, thio or C₁-C₄-alkylthio,    and to the plant-compatible acid addition salts or metal salts    thereof.

Furthermore, the invention relates to the use of the compounds of theformula I for controlling phytopathogenic fungi and to compositionscomprising these compounds.

Azolylmethyloxiranes, their preparation and their use in crop protectionare known, for example, from EP-A 0 094 564 and EP-A 0 196 038.

Azolylmethyloxiranes which carry a hetaryl substituent on the oxiranering are known from EP-A 0 421 125.

The azolylmethyloxiranes described already have good to very goodfungicidal activity against a number of pathogens; however, it was theobject of the present invention to provide novel azolylmethyloxiraneshaving improved fungicidal activity.

This object was achieved with the compounds of the formula I describedat the outset.

Owing to the basic character of their nitrogen atoms, the compound I iscapable of forming salts or adducts with inorganic or organic acids orwith metal ions.

Examples of inorganic acids are hydrohalic acids, such as hydrogenfluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide,carbonic acid, sulfuric acid, phosphoric acid and nitric acid.

Suitable organic acids are, for example, formic acid and alkanoic acids,such as acetic acid, trifluoroacetic acid, trichloroacetic acid andpropionic acid, and also glycolic acid, thiocyanic acid, lactic acid,succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid,alkylsulfonic acids (sulfonic acids having straight-chain or branchedalkyl radicals of 1 to 20 carbon atoms), arylsulfonic acids oraryldisulfonic acids (aromatic radicals, such as phenyl and naphthyl,which carry one or two sulfonic acid groups), alkylphosphonic acids(phosphonic acids having straight-chain or branched alkyl radicals of 1to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids(aromatic radicals, such as phenyl and naphthyl, which carry one or twophosphoric acid radicals), where the alkyl or aryl radicals may carryfurther substituents, for example p-toluenesulfonic acid, salicylicacid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoicacid, etc.

Suitable metal ions are in particular the ions of the elements of thesecond main group, in particular calcium and magnesium, of the third andfourth main group, in particular aluminum, tin and lead and also of theelements of transition groups one to eight, in particular chromium,manganese, iron, cobalt, nickel, copper, zinc, and others. Particularpreference is given to the metal ions of the elements of transitiongroups of the fourth period. The metals can be present in the variousvalencies that they can assume.

The preparation of the compounds of the formula I is known and describedin detail in EP-A 0 094 564, EP-A 0 196 038 and EP-A 0 421 125.

In the definitions of the symbols given in the formulae above,collective terms are used which are generally representative of thesubstituents below:

Halogen: fluorine, chlorine, bromine and iodine.

Alkyl and the alkyl moieties of composite groups such as, for example,alkylamino: saturated, straight-chain or branched hydrocarbon radicalshaving preferably 1 to 4 carbon atoms, such as methyl, ethyl, propyl,1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and1,1-dimethylethyl.

Haloalkyl: alkyl as mentioned above, where some or all of the hydrogenatoms in these groups are replaced by halogen atoms as mentioned above.In one embodiment, the alkyl groups are substituted at least once orcompletely by a particular halogen atom, preferably fluorine, chlorineor bromine. In a further embodiment, the alkyl groups are partially orfully halogenated by different halogen atoms; in the case of mixedhalogen substitutions, the combination of chlorine and fluorine ispreferred. Particular preference is given to (C₁-C₄)-haloalkyl, morepreferably (C₁-C₂)-haloalkyl, such as chloromethyl, bromomethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or1,1,1-trifluoroprop-2-yl.

Alkoxy: an alkyl group as defined above which is attached via an oxygen,preferably having 1 to 4 carbon atoms. Examples of preferred alkoxygroups are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy,1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy.

Haloalkoxy: alkoxy as defined above, where some or all of the hydrogenatoms in these groups are replaced by halogen atoms as described aboveunder haloalkyl, in particular fluorine, chlorine or bromine. Examplesof preferred haloalkoxy radicals are OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCHCl₂,OCCl₃, chlorofluoromethoxy, dichlorofluoromethoxy,chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy,2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC₂F₅,2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy,3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH₂—C₂F₅, OCF₂—C₂F₅,1-(CH₂F)-2-fluoroethoxy, 1-(CH₂Cl)-2-chloroethoxy,1-(CH₂Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxyor nonafluorobutoxy.

Alkylthio: alkyl as defined above which is attached via a sulfur atom.

5-membered heteroaryl which contains one, two, three or four nitrogenatoms or one, two or three nitrogen atoms and/or one sulfur or oxygenatom, where the heteroaryl may be attached via carbon or nitrogen, ifpresent: 5-membered heteroaryl groups which, in addition to carbonatoms, may contain one to four nitrogen atoms or one to three nitrogenatoms and/or one sulfur or oxygen atom as ring members, for examplefuryl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1,2,3-;1,2,4-triazolyl), tetrazolyl, oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl,thiazolyl, isothiazolyl and thiadiazolyl, in particular 2-furyl,3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl,4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl,5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl,4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl,2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl,1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl,1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;

6-membered heteroaryl which contains one, two, three or four, preferablyone, two or three, nitrogen atoms, where the heteroaryl may be attachedvia carbon or nitrogen, if present: 6-membered heteroaryl groups which,in addition to carbon atoms, may contain one to four or one to threenitrogen atoms as ring members, for example pyridinyl, pyrimidinyl,pyrazinyl, pyridazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, in particular 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.

The novel compounds of the formula I contain chiral centers and aregenerally obtained in the form of racemates or as diastereomer mixturesof erythro and threo forms. The erythro and threo diastereomers of thecompounds according to the invention can be separated and isolated inpure form, for example, on the basis of their different solubilities orby column chromatography. Using known methods, such uniform pairs ofdiastereomers can be used to obtain uniform enantiomers. Suitable foruse as antimicrobial agents are both the uniform diastereomers orenantiomers and mixtures thereof obtained in the synthesis. This appliescorrespondingly to the fungicidal compositions.

The compounds according to the invention may be present in variouscrystal modifications which may differ in their biological activity.They are likewise provided by the present invention.

In the compounds of the formula I according to the invention or in thecompounds of the formula I used according to the invention, thefollowing meanings of the substituents, in each case on their own or incombination, are particularly preferred. Here, the preferredsubstituents or preferred combinations of substituents apply, ifappropriate, correspondingly to the precursors of the compoundsaccording to the invention.

The substituent A or B is benzodioxolyl which is optionally substitutedby one to three of the following substituents: halogen, CN, NO₂, amino,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy,C₁-C₄-alkylamino, C₁-C₄-dialkylamino, thio or C₁-C₄-alkylthio.

According to one embodiment, benzodioxolyl is located in the3,4-position of the phenyl ring if it denotes substituent A.

According to a further embodiment, benzodioxolyl is located in the2,3-position of the phenyl ring if it denotes substituent B.

According to a further embodiment, A or B is benzodioxolyl which issubstituted by one to three further substituents selected from the groupconsisting of halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl andC₁-C₄-haloalkoxy.

According to another embodiment, the substituent A or B is benzodioxolylwhich is substituted by one to three further substituents selected fromthe group consisting of halogen, C₁-C₄-alkyl and C₁-C₄-alkoxy.

According to another embodiment, the substituent A or B is benzodioxolylwhich is substituted by one to three halogens.

In a preferred embodiment, the substituent A or B is benzodioxolyl whichis substituted by one or two further substituents selected from thegroup consisting of halogen.

In a further preferred embodiment, the substituent A or B isbenzodioxolyl which is substituted by two halogen in the dioxolyl ring.

In a further preferred embodiment, the substituent A or B isbenzodioxolyl which is substituted by two F in the dioxolyl ring.

In a preferred embodiment, the substituent A or B is benzodioxolyl whichis substituted in the dioxolyl ring by two F and in the phenyl ring by afurther substituent selected from the group consisting of F, Cl, methyland methoxy such that the substituents A1, B1 to A18, B18 of thefollowing formulae are obtained:

According to one embodiment, A is A1.

According to one embodiment, A is A2.

According to one embodiment, A is A3 where X=F.

According to one embodiment, A is A3 where X=Cl.

According to a further embodiment, A is A4 where X=F.

According to a further embodiment, A is A4 where X=Cl.

According to a further embodiment, A is A5 where X=F.

According to a further embodiment, A is A5 where X=Cl.

According to a further embodiment, A is A6.

According to a further embodiment, A is A7.

According to a further embodiment, A is A8.

According to a further embodiment, A is A9.

According to a further embodiment, A is A10.

According to a further embodiment, A is A11.

According to a further embodiment, A is A12 where X=F.

According to a further embodiment, A is A12 where X=Cl.

According to a further embodiment, A is A13 where X=F.

According to a further embodiment, A is A13 where X=Cl.

According to a preferred embodiment, A is A14 where X=F.

According to a preferred embodiment, A is A14 where X=Cl.

According to a further embodiment, A is A15.

According to a further embodiment, A is A16.

According to a further embodiment, A is A17.

According to a further embodiment, A is A18.

According to a further embodiment, A is A19.

According to a further embodiment, A is A20.

According to one embodiment, B is B1.

According to one embodiment, B is B2.

According to one embodiment, B is B3 where X=F.

According to one embodiment, B is B3 where X=Cl.

According to a further embodiment, B is B4 where X=F.

According to a further embodiment, B is B4 where X=Cl.

According to a further embodiment, B is B5 where X=F.

According to a further embodiment, B is B5 where X=Cl.

According to a further embodiment, B is B6.

According to a further embodiment, B is B7.

According to a further embodiment, B is B8.

According to a further embodiment, B is B9.

According to a further embodiment, B is B10.

According to a further embodiment, B is B11.

According to a further embodiment, B is B12 where X=F.

According to a further embodiment, B is B12 where X=Cl.

According to a further embodiment, B is B13 where X=F.

According to a further embodiment, B is B13 where X=Cl.

According to a preferred embodiment, B is B14 where X=F.

According to a preferred embodiment, B is B14 where X=Cl.

According to a further embodiment, B is B15.

According to a further embodiment, B is B16.

According to a further embodiment, B is B17.

According to a further embodiment, B is B18.

According to a particularly preferred embodiment, B is B19.

According to a further embodiment, B is B20.

In a further embodiment of the present invention, the respective othersubstituent A or B is phenyl which is substituted by one to three of thefollowing substituents: halogen, CN, NO₂, amino C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-alkylamino,C₁-C₄-dialkylamino, thio or C₁-C₄-alkylthio.

In a further embodiment, the respective other substituent A or B isphenyl which is substituted by one to three of the followingsubstituents: halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl orC₁-C₄-haloalkoxy.

In a preferred embodiment, the respective other substituent A or B isphenyl which is substituted by one to three halogen.

In a further embodiment, the respective other substituent A or B is a5-membered heteroaryl which is optionally substituted by one to three ofthe following substituents: halogen, CN, NO₂, amino, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-alkylamino,C₁-C₄-dialkylamino, thio or C₁-C₄-alkylthio.

In a further embodiment, the respective other substituent A or B is a5-membered heteroaryl selected from the group consisting of furyl,thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl,oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl andthiadiazolyl.

In a further embodiment, the respective other substituent A or B is a5-membered heteroaryl selected from the group consisting of furyl,thienyl, pyrrolyl, pyrazolyl, triazolyl and thiazolyl.

In a further embodiment, the respective other substituent A or B is a5-membered heteroaryl selected from the group consisting of thienyl,triazolyl and pyrazolyl.

In a further embodiment, the respective other substituent A or B is a5-membered heteroaryl which is substituted by one to three of thefollowing substituents: halogen, CN, NO₂, amino, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-alkylamino,C₁-C₄-dialkylamino, thio or C₁-C₄-alkylthio.

In a further embodiment, the respective other substituent A or B is a5-membered heteroaryl which is substituted by one to three of thefollowing substituents: halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy.

In a further embodiment, the respective other substituent A or B is a5-membered heteroaryl which is substituted by one to three of thefollowing substituents: halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy.

In a further embodiment, the respective other substituent A or B is a6-membered heteroaryl which is optionally substituted by one to three ofthe following substituents: halogen, CN, NO₂, amino, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-alkylamino,C₁-C₄-dialkylamino, thio or C₁-C₄-alkylthio.

In a further embodiment, the respective other substituent A or B is a6-membered heteroaryl selected from the group consisting of pyridinyl,pyrimidinyl, pyrazinyl, pyridazinyl, 1,2,3-triazinyl, 1,2,4-triazinyland 1,3,5-triazinyl.

In a further embodiment, the respective other substituent A or B is a6-membered heteroaryl selected from the group consisting of pyridyl andpyrimidinyl.

In a further embodiment, the respective other substituent A or B is a6-membered heteroaryl which is substituted by one to three of thefollowing substituents: halogen, NO₂, amino, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-alkylamino, C₁-C₄-dialkylamino,thio or C₁-C₄-alkylthio.

In a further embodiment, the respective other substituent A or B is a6-membered heteroaryl which is substituted by one to three of thefollowing substituents: halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy.

In a further embodiment, the respective other substituent A or B is a6-membered heteroaryl which is substituted by one to three of thefollowing substituents: halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy.

In particular with a view to their use, preference is given to thecompounds I according to the invention compiled in Tables 3 to 54 below.The groups mentioned for a substituent in the tables are furthermore perse, independently of the combination in which they are mentioned, aparticularly preferred embodiment of the substituent in question.

TABLE 1 Row Substituent B 1-1 2-methylphenyl 1-2 3-methylphenyl 1-34-methylphenyl 1-4 2-methoxyphenyl 1-5 3-methoxyphenyl 1-64-methoxyphenyl 1-7 2-chlorophenyl 1-8 3-chlorophenyl 1-9 4-chlorophenyl1-10 2-fluorophenyl 1-11 3-fluorophenyl 1-12 4-fluorophenyl 1-132-chloro-3-methoxyphenyl 1-14 2-chloro-4-methoxyphenyl 1-152,3-dichlorophenyl 1-16 2,4-dichlorophenyl 1-17 3,4-dichlorophenyl 1-182,3-difluorophenyl 1-19 2,4-difluorophenyl 1-20 2-chloro-3-fluorophenyl1-21 2-chloro-4-fluorophenyl 1-22 2-pyridinyl 1-23 3-pyridinyl 1-244-pyridinyl 1-25 2-chloropyridin-4-yl 1-26 3-chloropyridin-4-yl 1-272,6-dichloropyridin-4-yl 1-28 3,5-dichloropyridin-4-yl 1-293,6-dichloropyridin-4-yl 1-30 2-fluoropyridin-4-yl 1-313-fluoropyridin-4-yl 1-32 2-chloropyridin-3-yl 1-33 4-chloropyridin-3-yl1-34 5-chloropyridin-3-yl 1-35 6-chloropyridin-3-yl 1-362,4-dichloropyridin-3-yl 1-37 2,5-dichloropyridin-3-yl 1-382,6-dichloropyridin-3-yl 1-39 2-fluoropyridin-3-yl 1-404-fluoropyridin-3-yl 1-41 5-fluoropyridin-3-yl 1-42 6-fluoropyridin-3-yl1-43 3-chloropyridin-2-yl 1-44 4-chloropyridin-2-yl 1-455-chloropyridin-2-yl 1-46 6-chloropyridin-2-yl 1-47 3-fluoropyridin-2-yl1-48 4-fluoropyridin-2-yl 1-49 5-fluoropyridin-2-yl 1-506-fluoropyridin-2-yl 1-51 2-methylpyridin-4-yl 1-52 3-methylpyridin-4-yl1-53 2-methylpyridin-3-yl 1-54 4-methylpyridin-3-yl 1-555-methylpyridin-3-yl 1-56 6-methylpyridin-3-yl 1-57 3-methylpyridin-2-yl1-58 4-methylpyridin-2-yl 1-59 5-methylpyridin-2-yl 1-606-methylpyridin-2-yl 1-61 2-methoxypyridin-4-yl 1-623-methoxypyridin-4-yl 1-63 2-methoxypyridin-3-yl 1-644-methoxypyridin-3-yl 1-65 5-methoxypyridin-3-yl 1-666-methoxypyridin-3-yl 1-67 3-methoxypyridin-2-yl 1-684-methoxypyridin-2-yl 1-69 5-methoxypyridin-2-yl 1-706-methoxypyridin-2-yl 1-71 6-chloropyrimidin-3-yl 1-726-methylpyrimidin-3-yl 1-73 2-pyrimidinyl 1-74 4-pyrimidinyl 1-755-pyrimidinyl 1-76 6-methoxypyrimidin-3-yl 1-772,4-dichloropyrimidin-3-yl 1-78 2,6-dichloropyrimidin-3-yl 1-792,4-difluoropyrimidin-3-yl 1-80 2,6-difluoropyrimidin-3-yl 1-812-thienyl 1-82 3-thienyl 1-83 2-chlorothien-3-yl 1-84 4-chlorothien-3-yl1-85 5-chlorothien-3-yl 1-86 2,5-dichlorothien-3-yl 1-872,4,5-trichlorothien-3-yl 1-88 2-bromothien-3-yl 1-89 4-bromothien-3-yl1-90 5-bromothien-3-yl 1-91 2,5-dibromothien-3-yl 1-922,4,5-tribromothien-3-yl 1-93 3-pyrazolyl 1-94 4-pyrazolyl 1-951-methylpyrazol-3-yl 1-96 1-methylpyrazol-4-yl 1-97 1-methylpyrazol-5-yl1-98 2-imidazolyl 1-99 4-imidazolyl 1-100 1-methylimidazol-2-yl 1-1011-methylimidazol-4-yl 1-102 1-methylimidazol-5-yl 1-1031,5-dimethylimidazol-4-yl 1-104 1,2-dimethylimidazol-5-yl 1-1051,4-dimethylimidazol-5-yl

TABLE 2 Row Substituent A 2-1 2-methylphenyl 2-2 3-methylphenyl 2-34-methylphenyl 2-4 2-methoxyphenyl 2-5 3-methoxyphenyl 2-64-methoxyphenyl 2-7 2-chlorophenyl 2-8 3-chlorophenyl 2-9 4-chlorophenyl2-10 2-fluorophenyl 2-11 3-fluorophenyl 2-12 4-fluorophenyl 2-132-chloro-3-methoxyphenyl 2-14 2-chloro-4-methoxyphenyl 2-152,3-dichlorophenyl 2-16 2,4-dichlorophenyl 2-17 3,4-dichlorophenyl 2-182,3-difluorophenyl 2-19 2,4-difluorophenyl 2-20 2-chloro-3-fluorophenyl2-21 2-chloro-4-fluorophenyl 2-22 2-pyridinyl 2-23 3-pyridinyl 2-244-pyridinyl 2-25 2-chloropyridin-4-yl 2-26 3-chloropyridin-4-yl 2-272,6-dichloropyridin-4-yl 2-28 3,5-dichloropyridin-4-yl 2-293,6-dichloropyridin-4-yl 2-30 2-fluoropyridin-4-yl 2-313-fluoropyridin-4-yl 2-32 2-chloropyridin-3-yl 2-33 4-chloropyridin-3-yl2-34 5-chloropyridin-3-yl 2-35 6-chloropyridin-3-yl 2-362,4-dichloropyridin-3-yl 2-37 2,5-dichloropyridin-3-yl 2-382,6-dichloropyridin-3-yl 2-39 2-fluoropyridin-3-yl 2-404-fluoropyridin-3-yl 2-41 5-fluoropyridin-3-yl 2-42 6-fluoropyridin-3-yl2-43 3-chloropyridin-2-yl 2-44 4-chloropyridin-2-yl 2-455-chloropyridin-2-yl 2-46 6-chloropyridin-2-yl 2-47 3-fluoropyridin-2-yl2-48 4-fluoropyridin-2-yl 2-49 5-fluoropyridin-2-yl 2-506-fluoropyridin-2-yl 2-51 2-methylpyridin-4-yl 2-52 3-methylpyridin-4-yl2-53 2-methylpyridin-3-yl 2-54 4-methylpyridin-3-yl 2-555-methylpyridin-3-yl 2-56 6-methylpyridin-3-yl 2-57 3-methylpyridin-2-yl2-58 4-methylpyridin-2-yl 2-59 5-methylpyridin-2-yl 2-606-methylpyridin-2-yl 2-61 2-methoxypyridin-4-yl 2-623-methoxypyridin-4-yl 2-63 2-methoxypyridin-3-yl 2-644-methoxypyridin-3-yl 2-65 5-methoxypyridin-3-yl 2-666-methoxypyridin-3-yl 2-67 3-methoxypyridin-2-yl 2-684-methoxypyridin-2-yl 2-69 5-methoxypyridin-2-yl 2-706-methoxypyridin-2-yl 2-71 6-chloropyrimidin-3-yl 2-726-methylpyrimidin-3-yl 2-73 2-pyrimidinyl 2-74 4-pyrimidinyl 2-755-pyrimidinyl 2-76 6-methoxypyrimidin-3-yl 2-772,4-dichloropyrimidin-3-yl 2-78 2,6-dichloropyrimidin-3-yl 2-792,4-difluoropyrimidin-3-yl 2-80 2,6-difluoropyrimidin-3-yl 2-812-thienyl 2-82 3-thienyl 2-83 2-chlorothien-3-yl 2-84 4-chlorothien-3-yl2-85 5-chlorothien-3-yl 2-86 2,5-dichlorothien-3-yl 2-872,4,5-trichlorothien-3-yl 2-88 2-bromothien-3-yl 2-89 4-bromothien-3-yl2-90 5-bromothien-3-yl 2-91 2,5-dibromothien-3-yl 2-922,4,5-tribromothien-3-yl 2-93 3-pyrazolyl 2-94 4-pyrazolyl 2-951-methyl-pyrazol-3-yl 2-96 1-methyl-pyrazol-4-yl 2-971-methyl-pyrazol-5-yl 2-98 2-imidazolyl 2-99 4-imidazolyl 2-1001-methylimidazol-2-yl 2-101 1-methylimidazol-4-yl 2-1021-methylimidazol-5-yl 2-103 1,5-dimethylimidazol-4-yl 2-1041,2-dimethylimidazol-5-yl 2-105 1,4-dimethylimidazol-5-ylTable 3

-   -   Compounds of the formula I in which A is A1 and B corresponds in        each case to a substituent from a row of Table 1.        Table 4    -   Compounds of the formula I in which A is A2 and B corresponds in        each case to a substituent from a row of Table 1.        Table 5    -   Compounds of the formula I in which A is A3 where X=F and B        corresponds in each case to a substituent from a row of Table 1.        Table 6    -   Compounds of the formula I in which A is A3 where X=Cl and B        corresponds in each case to a substituent from a row of Table 1.        Table 7    -   Compounds of the formula I in which A is A4 where X=F and B        corresponds in each case to a substituent from a row of Table 1.        Table 8    -   Compounds of the formula I in which A is A4 where X=Cl and B        corresponds in each case to a substituent from a row of Table 1.        Table 9    -   Compounds of the formula I in which A is A5 where X=F and B        corresponds in each case to a substituent from a row of Table 1.        Table 10    -   Compounds of the formula I in which A is A5 where X=Cl and B        corresponds in each case to a substituent from a row of Table 1.        Table 11    -   Compounds of the formula I in which A is A6 and B corresponds in        each case to a substituent from a row of Table 1.        Table 12    -   Compounds of the formula I in which A is A7 and B corresponds in        each case to a substituent from a row of Table 1.        Table 13    -   Compounds of the formula I in which A is A8 and B corresponds in        each case to a substituent from a row of Table 1.        Table 14    -   Compounds of the formula I in which A is A9 and B corresponds in        each case to a substituent from a row of Table 1.        Table 15    -   Compounds of the formula I in which A is A10 and B corresponds        in each case to a substituent from a row of Table 1.        Table 16    -   Compounds of the formula I in which A is A11 and B corresponds        in each case to a substituent from a row of Table 1.        Table 17    -   Compounds of the formula I in which A is A12 where X=F and B        corresponds in each case to a substituent from a row of Table 1.        Table 18    -   Compounds of the formula I in which A is A12 where X=Cl and B        corresponds in each case to a substituent from a row of Table 1.        Table 19    -   Compounds of the formula I in which A is A13 where X=F and B        corresponds in each case to a substituent from a row of Table 1.        Table 20    -   Compounds of the formula I in which A is A13 where X=Cl and B        corresponds in each case to a substituent from a row of Table 1.        Table 21    -   Compounds of the formula I in which A is A14 where X=F and B        corresponds in each case to a substituent from a row of Table 1.        Table 22    -   Compounds of the formula I in which A is A14 where X=Cl and B        corresponds in each case to a substituent from a row of Table 1.        Table 23    -   Compounds of the formula I in which A is A15 and B corresponds        in each case to a substituent from a row of Table 1.        Table 24    -   Compounds of the formula I in which A is A16 and B corresponds        in each case to a substituent from a row of Table 1.        Table 25    -   Compounds of the formula I in which A is A17 and B corresponds        in each case to a substituent from a row of Table 1.        Table 26    -   Compounds of the formula I in which A is A18 and B corresponds        in each case to a substituent from a row of Table 1.        Table 27    -   Compounds of the formula I in which A is A19 and B corresponds        in each case to a substituent from a row of Table 1.        Table 28    -   Compounds of the formula I in which A is A20 and B corresponds        in each case to a substituent from a row of Table 1.        Table 29    -   Compounds of the formula I in which B is B1 and A corresponds in        each case to a substituent from a row of Table 2.        Table 30    -   Compounds of the formula I in which B is B2 and A corresponds in        each case to a substituent from a row of Table 2.        Table 31    -   Compounds of the formula I in which B is B3 where X=F and A        corresponds in each case to a substituent from a row of Table 2.        Table 32    -   Compounds of the formula I in which B is B3 where X=Cl and A        corresponds in each case to a substituent from a row of Table 2.        Table 33    -   Compounds of the formula I in which B is B4 where X=F and A        corresponds in each case to a substituent from a row of Table 2.        Table 34    -   Compounds of the formula I in which B is B4 where X=Cl and A        corresponds in each case to a substituent from a row of Table 2.        Table 35    -   Compounds of the formula I in which B is B5 where X=F and A        corresponds in each case to a substituent from a row of Table 2.        Table 36    -   Compounds of the formula I in which B is B5 where X=Cl and A        corresponds in each case to a substituent from a row of Table 2.        Table 37    -   Compounds of the formula I in which B is B6 and A corresponds in        each case to a substituent from a row of Table 2.        Table 38    -   Compounds of the formula I in which B is B7 and A corresponds in        each case to a substituent from a row of Table 2.        Table 39    -   Compounds of the formula I in which B is B8 and A corresponds in        each case to a substituent from a row of Table 2.        Table 40    -   Compounds of the formula I in which B is B9 and A corresponds in        each case to a substituent from a row of Table 2.        Table 41    -   Compounds of the formula I in which B is B10 and A corresponds        in each case to a substituent from a row of Table 2.        Table 42    -   Compounds of the formula I in which B is B11 and A corresponds        in each case to a substituent from a row of Table 2.        Table 43    -   Compounds of the formula I in which B is B12 where X=F and A        corresponds in each case to a substituent from a row of Table 2.        Table 44    -   Compounds of the formula I in which B is B12 where X=Cl and A        corresponds in each case to a substituent from a row of Table 2.        Table 45    -   Compounds of the formula I in which B is B13 where X=F and A        corresponds in each case to a substituent from a row of Table 2.        Table 46    -   Compounds of the formula I in which B is B13 where X=Cl and A        corresponds in each case to a substituent from a row of Table 2.        Table 47    -   Compounds of the formula I in which B is B14 where X=F and A        corresponds in each case to a substituent from a row of Table 2.        Table 48    -   Compounds of the formula I in which B is B14 where X=Cl and A        corresponds in each case to a substituent from a row of Table 2.        Table 49    -   Compounds of the formula I in which B is B15 and A corresponds        in each case to a substituent from a row of Table 2.        Table 50    -   Compounds of the formula I in which B is B16 and A corresponds        in each case to a substituent from a row of Table 2.        Table 51    -   Compounds of the formula I in which B is B17 and A corresponds        in each case to a substituent from a row of Table 2.        Table 52    -   Compounds of the formula I in which B is B18 and A corresponds        in each case to a substituent from a row of Table 2.        Table 53    -   Compounds of the formula I in which B is B19 and A corresponds        in each case to a substituent from a row of Table 2.        Table 54    -   Compounds of the formula I in which B is B20 and A corresponds        in each case to a substituent from a row of Table 2.

The compounds I are suitable as fungicides. They are distinguished by anexcellent activity against a broad spectrum of phytopathogenic fungifrom the class of the Ascomycetes, Deuteromycetes, Oomycetes andBasidiomycetes, in particular from the class of the Oomycetes. Some ofthem are systemically effective and can be used in crop protection asfoliar fungicides, as fungicides for seed dressing and as soilfungicides.

They are particularly important in the control of a multitude of fungion various crop plants, such as wheat, rye, barley, oats, rice, corn,grass, bananas, cotton, soya, coffee, sugar cane, vines, fruit andornamental plants, and vegetable plants, such as cucumbers, beans,tomatoes, potatoes and cucurbits, and on the seeds of these plants.

They are especially suitable for controlling the following plantdiseases:

-   -   Alternaria species on vegetables, oilseed rape, sugar beet and        fruit and rice, such as, for example, A. solani or A. alternata        on potatoes and tomatoes;    -   Aphanomyces species on sugar beet and vegetables;    -   Ascochyta species on cereals and vegetables;    -   Bipolaris and Drechslera species on corn, cereals, rice and        lawns, such as, for example, D. maydis on corn;    -   Blumeria graminis (powdery mildew) on cereals;    -   Botrytis cinerea (gray mold) on strawberries, vegetables,        flowers and grapevines;    -   Bremia lactucae on lettuce;    -   Cercospora species on corn, soybeans, rice and sugar beet;    -   Cochliobolus species on corn, cereals, rice, such as, for        example, Cochliobolus sativus on cereals, Cochliobolus        miyabeanus on rice;    -   Colletotricum species on soybeans and cotton;    -   Drechslera species, Pyrenophora species on corn, cereals, rice        and lawns, such as, for example, D. teres on barley or D.        tritici-repentis on wheat;    -   Esca on grapevines, caused by Phaeoacremonium chlamydosporium,        Ph. Aleophilum and Formitipora punctata (syn. Phellinus        punctatus);    -   Exserohilum species on corn;    -   Erysiphe cichoracearum and Sphaerotheca fuliginea on cucumber        plants;    -   Fusarium and Verticillium species on various plants, such as,        for example, F. graminearum or F. culmorum on cereals or F.        oxysporum on a multitude of plants, such as, for example,        tomatoes;    -   Gaeumanomyces graminis on cereals;    -   Gibberella species on cereals and rice (for example Gibberella        fujikuroi on rice);    -   Grainstaining complex on rice;    -   Helminthosporium species on corn and rice;    -   Michrodochium nivale on cereals;    -   Mycosphaerella species on cereals, bananas and groundnuts, such        as, for example, M. graminicola on wheat or M. fijiensis on        bananas;    -   Peronospora species on cabbage and bulbous plants, such as, for        example, P. brassicae on cabbage or P. destructor on onion;    -   Phakopsara pachyrhizi and Phakopsara meibomiae on soybeans;    -   Phomopsis species on soybeans and sunflowers;    -   Phytophthora infestans on potatoes and tomatoes;    -   Phytophthora species on various plants, such as, for example, P.        capsici on bell pepper;    -   Plasmopara viticola on grapevines;    -   Podosphaera leucotricha on apple;    -   Pseudocercosporella herpotrichoides on cereals;    -   Pseudoperonospora on various plants, such as, for example, P.        cubensis on cucumber or P. humili on hops;    -   Puccinia species on various plants, such as, for example, P.        triticina, P. striformins, P. hordei or P. graminis on cereals        or P. asparagi on asparagus;    -   Pyricularia oryzae, Corticium sasakii, Sarocladium oryzae, S.        attenuatum, Entyloma oryzae on rice;    -   Pyricularia grisea on lawns and cereals;    -   Pythium spp. on lawns, rice, corn, cotton, oilseed rape,        sunflowers, sugar beet, vegetables and other plants, such as,        for example, P. ultiumum on various plants, P. aphanidermatum on        lawns;    -   Rhizoctonia species on cotton, rice, potatoes, lawns, corn,        oilseed rape, potatoes, sugar beet, vegetables and on various        plants, such as, for example, R. solani on beet and various        plants;    -   Rhynchosporium secalis on barley, rye and triticale;    -   Sclerotinia species on oilseed rape and sunflowers;    -   Septoria tritici and Stagonospora nodorum on wheat;    -   Erysiphe (syn. Uncinula) necator on grapevines;    -   Setospaeria species on corn and lawns;    -   Sphacelotheca reilinia on corn;    -   Thievaliopsis species on soybeans and cotton;    -   Tilletia species on cereals;    -   Ustilago species on cereals, corn and sugar cane, such as, for        example, U. maydis on corn;    -   Venturia species (scab) on apples and pears, such as, for        example, V. inaequalis on apple.

They are particularly suitable for controlling harmful fungi from theclass of the Peronosporomycetes (syn. Oomycetes), such as Peronosporaspecies, Phytophthora species, Plasmopara viticola, Pseudoperonosporaspecies and Pythium species.

The compounds I are also suitable for controlling harmful fungi in theprotection of materials (for example wood, paper, paint dispersions,fibers or fabrics) and in the protection of stored products. In theprotection of wood, particular attention is paid to the followingharmful fungi: Ascomycetes, such as Ophiostoma spp., Ceratocystis spp.,Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicolaspp., Petriella spp., Trichurus spp.; Basidiomycetes, such as Coniophoraspp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp.,Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes, such asAspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp.,Alternaria spp., Paecilomyces spp. and Zygomycetes, such as Mucor spp.,additionally in the protection of materials the following yeasts:Candida spp. and Saccharomyces cerevisae.

The compounds I are employed by treating the fungi or the plants, seedsor materials to be protected against fungal attack or the soil with afungicidally effective amount of the active compounds. Application canbe both before and after the infection of the materials, plants or seedsby the fungi.

The fungicidal compositions generally comprise between 0.1 and 95% byweight, preferably between 0.5 and 90% by weight, of active compound.

When employed in crop protection, the application rates are, dependingon the kind of effect desired, between 0.01 and 2.0 kg of activecompound per ha.

In seed treatment, the amounts of active compound required are generallyfrom 1 to 1000 g/100 kg of seed, preferably from 5 to 100 g/100 kg ofseed.

When used in the protection of materials or stored products, the activecompound application rates depend on the kind of application area and onthe desired effect. Amounts typically applied in the protection ofmaterials are, for example, from 0.001 g to 2 kg, preferably from 0.005g to 1 kg, of active compound per cubic meter of treated material.

The compounds of the formula I can be present in different crystalmodifications which may differ in their biological activity. They arelikewise subject matter of the present invention.

The compounds I can be converted into the customary formulations, forexample solutions, emulsions, suspensions, dusts, powders, pastes andgranules. The application form depends on the particular purpose; ineach case, it should ensure a fine and uniform distribution of thecompound according to the invention.

The formulations are prepared in a known manner, for example byextending the active compound with solvents and/or carriers, if desiredusing emulsifiers and dispersants. Solvents/auxiliaries suitable forthis purpose are essentially:

-   -   water, aromatic solvents (for example Solvesso products,        xylene), paraffins (for example mineral oil fractions), alcohols        (for example methanol, butanol, pentanol, benzyl alcohol),        ketones (for example cyclohexanone, gamma-butyrolactone),        pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols,        fatty acid dimethylamides, fatty acids and fatty acid esters. In        principle, solvent mixtures may also be used,    -   carriers such as ground natural minerals (for example kaolins,        clays, talc, chalk) and ground synthetic minerals (for example        finely divided silica, silicates); emulsifiers such as        nonionogenic and anionic emulsifiers (for example        polyoxyethylene fatty alcohol ethers, alkylsulfonates and        arylsulfonates) and dispersants such as lignosulfite waste        liquors and methylcellulose.

Suitable for use as surfactants are alkali metal, alkaline earth metaland ammonium salts of lignosulfonic acid, naphthalenesulfonic acid,phenolsulfonic acid, dibutylnaphthalenesulfonic acid,alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcoholsulfates, fatty acids and sulfated fatty alcohol glycol ethers,furthermore condensates of sulfonated naphthalene and naphthalenederivatives with formaldehyde, condensates of naphthalene or ofnaphthalenesulfonic acid with phenol and formaldehyde, polyoxyethyleneoctylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol,alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether,tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcoholand fatty alcohol ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, laurylalcohol polyglycol ether acetal, sorbitol esters, lignosulfite wasteliquors and methylcellulose.

Suitable for the preparation of directly sprayable solutions, emulsions,pastes or oil dispersions are mineral oil fractions of medium to highboiling point, such as kerosene or diesel oil, furthermore coal tar oilsand oils of vegetable or animal origin, aliphatic, cyclic and aromatichydrocarbons, for example toluene, xylene, paraffin,tetrahydronaphthalene, alkylated naphthalenes or their derivatives,methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone,isophorone, strongly polar solvents, for example dimethyl sulfoxide,N-methylpyrrolidone and water.

Powders, materials for spreading and dustable products can be preparedby mixing or concomitantly grinding the active substances with a solidcarrier.

Granules, for example coated granules, impregnated granules andhomogeneous granules, can be prepared by binding the active compounds tosolid carriers. Examples of solid carriers are mineral earths such assilica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk,bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate,magnesium sulfate, magnesium oxide, ground synthetic materials,fertilizers, such as, for example, ammonium sulfate, ammonium phosphate,ammonium nitrate, ureas, and products of vegetable origin, such ascereal meal, tree bark meal, wood meal and nutshell meal, cellulosepowders and other solid carriers.

In general, the formulations comprise from 0.01 to 95% by weight,preferably from 0.1 to 90% by weight, of the active compound. The activecompounds are employed in a purity of from 90% to 100%, preferably 95%to 100% (according to NMR spectrum).

The following are examples of formulations: 1. Products for dilutionwith water

A Water-Soluble Concentrates (SL, LS)

10 parts by weight of the active compounds are dissolved with 90 partsby weight of water or with a water-soluble solvent. As an alternative,wetters or other auxiliaries are added. The active compound dissolvesupon dilution with water. This gives a formulation having an activecompound content of 10% by weight.

B Dispersible Concentrates (DC)

20 parts by weight of the active compounds are dissolved in 70 parts byweight of cyclohexanone with addition of 10 parts by weight of adispersant, for example polyvinylpyrrolidone. Dilution with water givesa dispersion. The active compound content is 20% by weight.

C Emulsifiable Concentrates (EC)

15 parts by weight of the active compounds are dissolved in 75 parts byweight of xylene with addition of calcium dodecylbenzenesulfonate andcastor oil ethoxylate (in each case 5 parts by weight). Dilution withwater gives an emulsion. The formulation has an active compound contentof 15% by weight.

D Emulsions (EW, EO, ES)

25 parts by weight of the active compounds are dissolved in 35 parts byweight of xylene with addition of calcium dodecylbenzenesulfonate andcastor oil ethoxylate (in each case 5 parts by weight). This mixture isadded to 30 parts by weight of water by means of an emulsifying machine(e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution withwater gives an emulsion. The formulation has an active compound contentof 25% by weight.

E Suspensions (SC, OD, FS)

In an agitated ball mill, 20 parts by weight of the active compounds arecomminuted with addition of 10 parts by weight of dispersants andwetters and 70 parts by weight of water or an organic solvent to give afine active compound suspension. Dilution with water gives a stablesuspension of the active compound. The active compound content in theformulation is 20% by weight.

F Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50 parts by weight of the active compounds are ground finely withaddition of 50 parts by weight of dispersants and wetters and made intowater-dispersible or water-soluble granules by means of technicalappliances (for example extrusion, spray tower, fluidized bed). Dilutionwith water gives a stable dispersion or solution of the active compound.The formulation has an active compound content of 50% by weight.

G Water-Dispersible Powders and Water-Soluble Powders (WP, SP, SS, WS)

75 parts by weight of the active compounds are ground in a rotor-statormill with addition of 25 parts by weight of dispersants, wetters andsilica gel. Dilution with water gives a stable dispersion or solution ofthe active compound. The active compound content of the formulation is75% by weight.

H Gel Formulations (GF)

20 parts by weight of the active compounds, 10 parts by weight ofdispersant, 1 part by weight of gelling agent and 70 parts by weight ofwater or an organic solvent are ground in a ball mill to give a finesuspension. Dilution with water gives a stable suspension with an activecompound content of 20% by weight.

2. Products to be Applied Undiluted

I Dusts (DP, DS)

5 parts by weight of the active compounds are ground finely and mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dustable product with an active compound content of 5% by weight.

J Granules (GR, FG, GG, MG)

0.5 part by weight of the active compounds is ground finely andassociated with 99.5 parts by weight of carriers. Current methods areextrusion, spray-drying or the fluidized bed. This gives granules withan active compound content of 0.5% by weight to be applied undiluted.

K ULV Solutions (UL)

10 parts by weight of the active compounds are dissolved in 90 parts byweight of an organic solvent, for example xylene. This gives a productwith an active compound content of 10% by weight to be appliedundiluted.

Water-soluble concentrates (LS), suspensions (FS), dusts (DS),water-dispersible and water-soluble powders (WS, SS), emulsions (ES),emulsifiable concentrates (EC) and gel formulations (GF) are usuallyused for the treatment of seed. These formulations can be applied to theseed in undiluted or, preferably, diluted form. The application can becarried out before sowing.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, for example in theform of directly sprayable solutions, powders, suspensions ordispersions, emulsions, oil dispersions, pastes, dustable products,materials for spreading, or granules, by means of spraying, atomizing,dusting, spreading or pouring. The use forms depend entirely on theintended purposes; the intention is to ensure in each case the finestpossible distribution of the active compounds according to theinvention.

Aqueous use forms can be prepared from emulsion concentrates, pastes orwettable powders (sprayable powders, oil dispersions) by adding water.To prepare emulsions, pastes or oil dispersions, the substances, as suchor dissolved in an oil or solvent, can be homogenized in water by meansof a wetter, tackifier, dispersant or emulsifier. Alternatively, it ispossible to prepare concentrates composed of active substance, wetter,tackifier, dispersant or emulsifier and, if appropriate, solvent or oil,and such concentrates are suitable for dilution with water.

The active compound concentrations in the ready-to-use preparations canbe varied within relatively wide ranges. In general, they are from0.0001 to 10%, preferably from 0.01 to 1%.

The active compounds may also be used successfully in theultra-low-volume process (ULV), by which it is possible to applyformulations comprising over 95% by weight of active compound, or evento apply the active compound without additives.

Various types of oils, wetters, adjuvants, herbicides, fungicides, otherpesticides, or bactericides may be added to the active compounds, ifappropriate not until immediately prior to use (tank mix). Thesecompositions can be admixed with the compositions according to theinvention in a weight ratio of from 1:100 to 100:1, preferably from 1:10to 10:1.

The following are particularly suitable as adjuvants in this context:organically modified polysiloxanes, for example Break Thru S 240®;alcohol alkoxylates, for example Atplus 245®, Atplus MBA 1303®, PlurafacLF 300® and Lutensol ON 30®; EO-PO block polymers, for example PluronicRPE 2035® and Genapol B®; alcohol ethoxylates, for example Lutensol XP80®; and sodium dioctylsulfosuccinate, for example Leophen RA®.

The compositions according to the invention in the application form asfungicides can also be present together with other active compounds, forexample with herbicides, insecticides, growth regulators, fungicides orelse with fertilizers. When mixing the compounds I or the compositionscomprising them with one or more further active compounds, in particularfungicides, it is in many cases possible, for example, to widen theactivity spectrum or to prevent the development of resistance. In manycases, synergistic effects are obtained.

The present invention furthermore provides a combination of at least oneazolylmethyloxirane of the formula I, in particular anazolylmethyloxirane disclosed in the present description as beingpreferred, and/or an agriculturally acceptable salt thereof and at leastone further fungicidal, insecticidal, herbicidal and/orgrowth-regulating active compound, it being possible for a synergisticeffect to occur.

The present invention also provides a pesticidal composition whichcomprises at least one compound of the formula I, in particular acompound of the formula I described in the present description as beingpreferred, and/or an agriculturally acceptable acid addition salt ormetal salt thereof and at least one solid or liquid carrier. Such apesticidal composition may comprise at least one further fungicidally,insecticidally and/or herbicidally active compound, it also beingpossible for a synergistic effect to occur.

The following list L of fungicides with which the compounds according tothe invention can be applied together is meant to illustrate thepossible combinations, but not to limit them:

List L:

Strobilurins

azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin,kresoxim-methyl, methominostrobin, orysastrobin, picoxystrobin,pyraclostrobin, pyribencarb, trifloxystrobin,2-(2-(6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yloxy)phenyl)-2-methoxyimino-N-methylacetamide,methyl2-(ortho-((2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate,methyl3-methoxy-2-(2-(N-(4-methoxyphenyl)cyclopropanecarboximidoylsulfanylmethyl)phenyl)acrylate;

Carboxamides

carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid,carboxin, fenfuram, fenhexamid, flutolanil, furametpyr, isotianil,kiralaxyl, mepronil, metalaxyl, ofurace, oxadixyl, oxycarboxin,penthiopyrad, tecloftalam, thifluzamide, tiadinil,2-amino-4-methylthiazole-5-carboxanilide,2-chloro-N-(1,1,3-trimethylindan-4-yl)-nicotinamide,N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,N-(4′-chloro-3′,5-difluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,N-(4′-chloro-3′,5-difluorobiphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,N-(3′,5-difluoro-4′-methylbiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,N-(3′,5-difluoro-4′-methylbiphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,N-(2-bicyclopropyl-2-ylphenyl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,N-(cis-2-bicyclopropyl-2-ylphenyl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,N-(trans-2-bicyclopropyl-2-ylphenyl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,

carboxylic acid morpholides: dimethomorph, flumorph;

benzamides: flumetover, fluopicolide, fluopyram, zoxamide,N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxybenzamide;

other carboxamides: carpropamid, diclocymet, mandipropamid,oxytetracyclin, silthiofam,N-(6-methoxypyridin-3-yl)cyclopropanecarboxamide;

Azoles

triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole,difenoconazole, diniconazole, diniconazole-M, epoxiconazole,fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole,imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole,paclobutrazole, penconazole, propiconazole, prothioconazole,simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol,triticonazole, uniconazole,1-(4-chlorophenyl)-2-([1,2,4]triazol-1-yl)-cycloheptanol;

imidazoles: cyazofamid, imazalil, imazalil sulfate, pefurazoate,prochloraz, triflumizole;

benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;

others: ethaboxam, etridiazole, hymexazole,1-(4-chlorophenyl)-1-(propyn-2-yloxy)-3-(4-(3,4-dimethoxyphenyl)isoxazol-5-yl)propan-2-one;

Nitrogenous Heterocyclyl Compounds

pyridines: fluazinam, pyrifenox,3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]-pyridine,2,3,5,6-tetrachloro-4-methanesulfonylpyridine,3,4,5-trichloropyridine-2,6-dicarbonitrile,N-(1-(5-bromo-3-chloropyridin-2-yl)ethyl)-2,4-dichloronicotinamide,N-((5-bromo-3-chloropyridin-2-yl)methyl)-2,4-dichloronicotinamide;

pyrimidines: bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone,mepanipyrim, nitrapyrin, nuarimol, pyrimethanil;

pyrroles: fludioxonil, fenpiclonil;

morpholines: aldimorph, dodemorph, dodemorph acetate, fenpropimorph,tridemorph;

dicarboximides: fluoroimide, iprodione, procymidone, vinclozolin;

others: acibenzolar-5-methyl, amisulbrom, anilazine, blasticidin-S,captafol, captan, quinomethionate, dazomet, debacarb, diclomezine,difenzoquat, difenzoquat methylsulfate, famoxadone, fenamidone,fenoxanil, fenpropidin, folpet, octhilinone, oxolinic acid, piperalin,probenazole, proquinazid, pyroquilon, quinoxyfen, triazoxide,tricyclazole, triforine,5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine,2-butoxy-6-iodo-3-propylchromen-4-one; carbamates and dithiocarbamates

thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam,methasulfocarb, metiram, propineb, thiram, zineb, ziram;

carbamates: diethofencarb, benthiavalicarb, iprovalicarb, propamocarb,propamocarb hydrochloride, valiphenal, 4-fluorophenylN-(1-(1-(4-cyanophenyl)-ethanesulfonyl)but-2-yl)carbamate;

Other Fungicides

guanidines: dodine, dodine free base, guazatine, guazatine acetate,iminoctadine, iminoctadine-triacetate, iminoctadine tris(albesilate);

antibiotics: kasugamycin, kasugamycin hydrochloride hydrate, polyoxins,streptomycin, validamycin A;

nitrophenyl derivatives:

binapacryl, dicloran, dinobuton, dinocap, nitrothal-isopropyl, tecnazen;

organometallic compounds: fentin salts such as, for example, fentinacetate, fentin chloride, fentin hydroxide;

sulfur-containing heterocyclyl compounds: isoprothiolane, dithianon;

organophosphorus compounds: edifenphos, fosetyl, fosetyl aluminum,iprobenfos, pyrazophos, tolclofos methyl;

organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen,flusulfamide, hexachlorobenzene, pencycuron, pentachlorophenol and saltsthereof, phthalide, quintozene, thiophanate methyl, tolylfluanid,N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide;

inorganic active compounds: phosphorous acid and salts thereof, sulfur,Bordeaux mixture, copper salts such as, for example, copper acetate,copper hydroxide, copper oxychloride, basic copper sulfate;

others: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine,metrafenone, mildiomycin, oxine-copper, prohexadione-calcium,spiroxamine, tolylfluanid,N-(cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluorophenyl)methyl)-2-phenylacetamide,N′-(4-(4-chloro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methylformamidine,N′-(4-(4-fluoro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methylformamidine,N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanylpropoxy)phenyl)-N-ethyl-N-methylformamidine,N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanylpropoxy)phenyl)-N-ethyl-N-methylformamidine.

The present invention further relates, accordingly, to the compositionsthat are listed in table B, each line of table B corresponding to afungicidal composition comprising a compound of the formula I (component1), which is preferably one of the compounds described herein as beingpreferred, and comprising the further active compound indicated in eachcase in the line in question (component 2). According to one embodimentof the invention, component 1 in each line of table B is in each caseone of the compounds of the formula I that are specificallyindividualized in tables 1 to 54.

TABLE B Line Component 1 Component 2 B-1 a compound of the formula Iazoxystrobin B-2 a compound of the formula I dimoxystrobin B-3 acompound of the formula I enestroburin B-4 a compound of the formula Ifluoxastrobin B-5 a compound of the formula I kresoxim-methyl B-6 acompound of the formula I metominostrobin B-7 a compound of the formulaI orysastrobin B-8 a compound of the formula I picoxystrobin B-9 acompound of the formula I pyraclostrobin B-10 a compound of the formulaI pyribencarb B-11 a compound of the formula I trifloxystrobin B-12 acompound of the formula I 2-(2-(6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yloxy)phenyl)- 2-methoxyimino-N-methylacetamide B-13a compound of the formula I methyl 2-(ortho-((2,5-dimethylphenyloxy-methylene)phenyl)-3-methoxyacrylate B-14 a compound of the formula Imethyl 3-methoxy-2-(2-(N-(4-methoxyphenyl)-cyclopropanecarboximidoylsulfanyl- methyl)phenyl)acrylate B-15 acompound of the formula I benalaxyl B-16 a compound of the formula Ibenalaxyl-M B-17 a compound of the formula I benodanil B-18 a compoundof the formula I bixafen B-19 a compound of the formula I boscalid B-20a compound of the formula I carboxin B-21 a compound of the formula Ifenfuram B-22 a compound of the formula I fenhexamid B-23 a compound ofthe formula I flutolanil B-24 a compound of the formula I furametpyrB-25 a compound of the formula I isotianil B-26 a compound of theformula I kiralaxyl B-27 a compound of the formula I mepronil B-28 acompound of the formula I metalaxyl B-29 a compound of the formula Iofurace B-30 a compound of the formula I oxadixyl B-31 a compound of theformula I oxycarboxin B-32 a compound of the formula I penthiopyrad B-33a compound of the formula I thifluzamide B-34 a compound of the formulaI tecloftalam B-35 a compound of the formula I tiadinil B-36 a compoundof the formula I 2-amino-4-methylthiazole-5-carboxanilide B-37 acompound of the formula I 2-chloro-N-(1,1,3-trimethylindan-4-yl)-nicotinamide B-38 a compound of the formula IN-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole- 4-carboxamide B-39 a compound ofthe formula I 5-fluoro-1,3-dimethyl-1H-pyrazole- 4-carboxylic acid[2-(1,3-dimethylbutyl)- phenyl]amide B-40 a compound of the formula IN-(4′-chloro-3′,5-difluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole- 4-carboxamide B-41 a compound ofthe formula I N-(4′-chloro-3′,5-difluorobiphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole- 4-carboxamide B-42 a compound ofthe formula I N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole- 4-carboxamide B-43 a compound ofthe formula I N-(3′,5-difluoro-4′-methylbiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole- 4-carboxamide B-44 a compound ofthe formula I N-(3′,5-difluoro-4′-methylbiphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole- 4-carboxamide B-45 a compound ofthe formula I N-(2-bicyclopropyl-2-yl-phenyl)-3-difluoro-methyl-1-methyl-1H-pyrazole-4-carboxamide B-46 a compound of the formulaI N-(cis-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1-methyl-1H-pyrazole- 4-carboxamide B-47 a compound ofthe formula I N-(trans-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1-methyl-1H-pyrazole- 4-carboxamide B-48 a compound ofthe formula I dimethomorph B-49 a compound of the formula I flumorphB-50 a compound of the formula I flumetover B-51 a compound of theformula I fluopicolide (picobenzamid) B-52 a compound of the formula Ifluopyram B-53 a compound of the formula I zoxamide B-54 a compound ofthe formula I N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxybenzamide B-55 a compound of the formula Icarpropamid B-56 a compound of the formula I diclocymet B-57 a compoundof the formula I mandipropamid B-58 a compound of the formula Ioxytetracyclin B-59 a compound of the formula I silthiofam B-60 acompound of the formula I N-(6-methoxypyridin-3-yl)cyclopropane-carboxamide B-61 a compound of the formula I azaconazole B-62 a compoundof the formula I bitertanol B-63 a compound of the formula Ibromuconazole B-64 a compound of the formula I cyproconazole B-65 acompound of the formula I difenoconazole B-66 a compound of the formulaI diniconazole B-67 a compound of the formula I diniconazole-M B-68 acompound of the formula I enilconazole B-69 a compound of the formula Iepoxiconazole B-70 a compound of the formula I fenbuconazole B-71 acompound of the formula I flusilazole B-72 a compound of the formula Ifluquinconazole B-73 a compound of the formula I flutriafol B-74 acompound of the formula I hexaconazole B-75 a compound of the formula Iimibenconazole B-76 a compound of the formula I ipconazole B-77 acompound of the formula I metconazole B-78 a compound of the formula Imyclobutanil B-79 a compound of the formula I oxpoconazole B-80 acompound of the formula I paclobutrazole B-81 a compound of the formulaI penconazole B-82 a compound of the formula I propiconazole B-83 acompound of the formula I prothioconazole B-84 a compound of the formulaI simeconazole B-85 a compound of the formula I tebuconazole B-86 acompound of the formula I tetraconazole B-87 a compound of the formula Itriadimenol B-88 a compound of the formula I triadimefon B-89 a compoundof the formula I triticonazole B-90 a compound of the formula Iuniconazole B-91 a compound of the formula I1-(4-chlorophenyl)-2-([1,2,4]triazol-1-yl)- cycloheptanol B-92 acompound of the formula I cyazofamid B-93 a compound of the formula Iimazalil B-94 a compound of the formula I imazalil sulfate B-95 acompound of the formula I pefurazoate B-96 a compound of the formula Iprochloraz B-97 a compound of the formula I triflumizole B-98 a compoundof the formula I benomyl B-99 a compound of the formula I carbendazimB-100 a compound of the formula I fuberidazole B-101 a compound of theformula I thiabendazole B-102 a compound of the formula I ethaboxamB-103 a compound of the formula I etridiazole B-104 a compound of theformula I hymexazole B-105 a compound of the formula I fluazinam B-106 acompound of the formula I pyrifenox B-107 a compound of the formula I1-(4-chlorophenyl)-1-(propyn-2-yloxy)-3-(4-(3,4-dimethoxyphenyl)isoxazol-5-yl)- propan-2-one B-108 a compoundof the formula I 3-[5-(4-chlorophenyl)-2,3-dimethyl-isoxazolidin-3-yl]pyridine B-109 a compound of the formula I2,3,5,6-tetrachloro-4-methanesulfonyl- pyridine B-110 a compound of theformula I 3,4,5-trichloropyridine-2,6-dicarbonitrile B-111 a compound ofthe formula I N-(1-(5-bromo-3-chloropyridin-2-yl)ethyl)-2,4-dichloronicotinamide B-112 a compound of the formula IN-((5-bromo-3-chloropyridin-2-yl)methyl)- 2,4-dichloronicotinamide B-113a compound of the formula I bupirimate B-114 a compound of the formula Icyprodinil B-115 a compound of the formula I diflumetorim B-116 acompound of the formula I ferimzone B-117 a compound of the formula Ifenarimol B-118 a compound of the formula I mepanipyrim B-119 a compoundof the formula I nitrapyrin B-120 a compound of the formula I nuarimolB-121 a compound of the formula I pyrimethanil B-122 a compound of theformula I fludioxonil B-123 a compound of the formula I fenpiclonilB-124 a compound of the formula I aldimorph B-125 a compound of theformula I dodemorph B-126 a compound of the formula I dodemorph acetateB-127 a compound of the formula I fenpropimorph B-128 a compound of theformula I tridemorph B-129 a compound of the formula I fluoroimide B-130a compound of the formula I iprodione B-131 a compound of the formula Iprocymidone B-132 a compound of the formula I vinclozolin B-133 acompound of the formula I acibenzolar-S-methyl B-134 a compound of theformula I amisulbrom B-135 a compound of the formula I anilazine B-136 acompound of the formula I blasticidin-S B-137 a compound of the formulaI captan B-138 a compound of the formula I captafol B-139 a compound ofthe formula I chinomethionat B-140 a compound of the formula I dazometB-141 a compound of the formula I debacarb B-142 a compound of theformula I diclomezine B-143 a compound of the formula I difenzoquatB-144 a compound of the formula I difenzoquat methylsulfate B-145 acompound of the formula I famoxadone B-146 a compound of the formula Ifenamidone B-147 a compound of the formula I fenoxanil B-148 a compoundof the formula I fenpropidin B-149 a compound of the formula I folpetB-150 a compound of the formula I octhilinone B-151 a compound of theformula I oxolinic acid B-152 a compound of the formula I piperalinB-153 a compound of the formula I probenazole B-154 a compound of theformula I proquinazid B-155 a compound of the formula I pyroquilon B-156a compound of the formula I quinoxyfen B-157 a compound of the formula Itriazoxide B-158 a compound of the formula I tricyclazole B-159 acompound of the formula I triforine B-160 a compound of the formula I5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo- [1,5-a]pyrimidine B-161 acompound of the formula I 2-butoxy-6-iodo-3-propylchromen-4-one B-162 acompound of the formula I ferbam B-163 a compound of the formula Imancozeb B-164 a compound of the formula I maneb B-165 a compound of theformula I metiram B-166 a compound of the formula I metam B-167 acompound of the formula I methasulfocarb B-168 a compound of the formulaI propineb B-169 a compound of the formula I thiram B-170 a compound ofthe formula I zineb B-171 a compound of the formula I ziram B-172 acompound of the formula I diethofencarb B-173 a compound of the formulaI flubenthiavalicarb B-174 a compound of the formula I iprovalicarbB-175 a compound of the formula I propamocarb B-176 a compound of theformula I propamocarb hydrochloride B-177 a compound of the formula Imethyl 3-(4-chlorophenyl)-3-(2-isopropoxy-carbonylamino-3-methylbutyrylamino)- propionate B-178 a compound of theformula I valiphenal B-179 a compound of the formula I 4-fluorophenylN-(1-(1-(4-cyanophenyl)- ethanesulfonyl)but-2-yl)carbamate B-180 acompound of the formula I dodine B-181 a compound of the formula Idodine free base B-182 a compound of the formula I iminoctadine B-183 acompound of the formula I iminoctadine triacetate B-184 a compound ofthe formula I iminoctadine tris(albesilate) B-185 a compound of theformula I guazatine B-186 a compound of the formula I guazatine acetateB-187 a compound of the formula I kasugamycin B-188 a compound of theformula I kasugamycin hydrochloride hydrate B-189 a compound of theformula I polyoxine B-190 a compound of the formula I streptomycin B-191a compound of the formula I validamycin A B-192 a compound of theformula I binapacryl B-193 a compound of the formula I dicloran B-194 acompound of the formula I dinobuton B-195 a compound of the formula Idinocap B-196 a compound of the formula I nitrothal-isopropyl B-197 acompound of the formula I tecnazen B-198 a compound of the formula Ifentin acetate B-199 a compound of the formula I fentin chloride B-200 acompound of the formula I fentin hydroxide B-201 a compound of theformula I isoprothiolane B-202 a compound of the formula I dithianonB-203 a compound of the formula I edifenphos B-204 a compound of theformula I fosetyl B-205 a compound of the formula I fosetyl aluminumB-206 a compound of the formula I iprobenfos B-207 a compound of theformula I pyrazophos B-208 a compound of the formula I tolclofos-methylB-209 a compound of the formula I chlorothalonil B-210 a compound of theformula I dichlofluanid B-211 a compound of the formula I dichlorophenB-212 a compound of the formula I flusulfamide B-213 a compound of theformula I hexachlorobenzene B-214 a compound of the formula I pencycuronB-215 a compound of the formula I pentachlorophenol and salts thereofB-216 a compound of the formula I phthalide B-217 a compound of theformula I quintozene B-218 a compound of the formula I thiophanatemethyl B-219 a compound of the formula I tolylfluanid B-220 a compoundof the formula I N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide B-221 a compound of the formula I phosphorousacid and salts thereof B-222 a compound of the formula I sulfur B-223 acompound of the formula I Bordeaux mixture B-224 a compound of theformula I copper acetate B-225 a compound of the formula I copperhydroxide B-226 a compound of the formula I copper oxychloride B-227 acompound of the formula I basic copper sulfate B-228 a compound of theformula I biphenyl B-229 a compound of the formula I bronopol B-230 acompound of the formula I cyflufenamid B-231 a compound of the formula Icymoxanil B-232 a compound of the formula I diphenylamine B-233 acompound of the formula I metrafenone B-234 a compound of the formula Imildiomycin B-235 a compound of the formula I oxine-copper B-236 acompound of the formula I prohexadione-calcium B-237 a compound of theformula I spiroxamine B-238 a compound of the formula I tolylfluanidB-239 a compound of the formula IN-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluorophenyl)-methyl)- 2-phenylacetamide B-240 a compoundof the formula I N′-(4-(4-chloro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methyl- formamidine B-241 a compound ofthe formula I N′-(4-(4-fluoro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methyl- formamidine B-242 a compound ofthe formula I N′-(2-methyl-5-trifluoromethyl-4-(3-tri-methylsilanylpropoxy)phenyl)-N-ethyl- N-methylformamidine B-243 acompound of the formula I N′-(5-difluoromethyl-2-methyl-4-(3-tri-methylsilanylpropoxy)phenyl)-N-ethyl- N-methylformamidine

The active compounds II specified above as component 2, theirpreparation, and their effect against fungal pathogens are widely known;they are available commercially. The compounds with IUPAC nomenclature,their preparation, and their fungicidal activity are likewise known [cf.EP-A 226 917; EP-A 10 28 125; EP-A 10 35 122; EP-A 12 01 648; WO98/46608; WO 99/24413; WO 03/14103; WO 03/053145; WO 03/066609; WO04/049804].

SYNTHESIS EXAMPLES

Prepared was the active compound1-[3-(2,2-difluorobenzo[1,3]dioxol-5-yl)-2-(4-fluoro-phenyl)oxiranylmethyl]-1H-[1,2,4]triazolehaving the following physical properties:

H-NMR (CDCl3, 300 MHz): 7.78-7.82 (2H), 7.32-7.00 (7H), 4.68 (1H),4.18-4.13 (2H).

1. A compound of formula I

wherein A or B is benzodioxolyl which is substituted by one to five ofthe following substituents: halogen, CN, NO₂, amino, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-alkylamino,C₁-C₄-dialkylamino, thio or C₁-C₄-alkylthio, and the respective othersubstituent A or B is phenyl or 5-membered or 6-membered heteroaryl,these substituents optionally being substituted by one to three of thefollowing substituents: halogen, CN, NO₂, amino, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-alkylamino,C₁-C₄-dialkylamino, thio or C₁-C₄-alkylthio, or a plant-compatible acidaddition salt or metal salt thereof.
 2. The compound of claim 1, whereinsaid benzodioxolyl is substituted by one to five of the followingsubstituents: halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl orC₁-C₄-haloalkoxy.
 3. The compound of claim 2, wherein said benzodioxolylis substituted by one to five of the following substituents: halogen,C₁-C₄-alkyl or C₁-C₄-alkoxy.
 4. The compound of claim 2, wherein saidbenzodioxolyl is substituted by two halogen in the dioxolyl ring.
 5. Thecompound of claim 4, wherein said benzodioxolyl is substituted by one tofive halogen.
 6. The compound of claim 1, wherein said phenyl issubstituted by one to three of the following substituents: halogen, CN,NO₂, amino, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl,C₁-C₄-haloalkoxy, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, thio orC₁-C₄-alkylthio.
 7. The compound of claim 1, wherein said phenyl issubstituted by one to three of the following substituents: halogen,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy.
 8. Thecompound of claim 1, wherein said phenyl is substituted by one to threeof the following substituents: halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy. 9.The compound of claim 1, wherein said 5-membered heteroaryl is selectedfrom the group consisting of furyl, thienyl, pyrrolyl, pyrazolyl,imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl,1,3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl.
 10. Thecompound of claim 9, wherein said 5-membered heteroaryl is selected fromthe group consisting of furyl, thienyl, pyrrolyl, pyrazolyl, triazolyland thiazolyl.
 11. The compound of claim 10, wherein said 5-memberedheteroaryl is selected from the group consisting of thienyl, triazolyland pyrazolyl.
 12. The compound of claim 1, wherein said 6-memberedheteroaryl is selected from the group consisting of pyridinyl,pyrimidinyl, pyrazinyl, pyridazinyl, 1,2,3-triazinyl, 1,2,4-triazinyland 1,3,5-triazinyl.
 13. The compound of claim 12, wherein said6-membered heteroaryl is selected from the group consisting of pyridyland pyrimidinyl.
 14. A crop protection composition comprising a solid orliquid carrier and a compound of formula I of claim 1 and/or an acidaddition salt or metal salt thereof.
 15. Seed comprising at least onecompound of formula I of claim 1 and/or an acid addition salt or metalsalt thereof.
 16. A method for controlling phytopathogenic fungi whereinthe fungi or the materials, plants, the soil or seed to be protectedagainst fungal attack are/is treated with an effective amount of acompound of formula I of claim 1 or an acid addition salt or metal saltthereof.